CN108933197A - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
- Publication number
- CN108933197A CN108933197A CN201810495632.8A CN201810495632A CN108933197A CN 108933197 A CN108933197 A CN 108933197A CN 201810495632 A CN201810495632 A CN 201810495632A CN 108933197 A CN108933197 A CN 108933197A
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- Prior art keywords
- layer
- electron
- electrode
- organic electroluminescence
- electroluminescence device
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 37
- 239000002019 doping agent Substances 0.000 claims abstract description 80
- 230000002708 enhancing effect Effects 0.000 claims abstract description 65
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims description 76
- 230000005540 biological transmission Effects 0.000 claims description 51
- 229910052751 metal Inorganic materials 0.000 claims description 45
- -1 perfluoro alkane Chemical class 0.000 claims description 44
- 239000002184 metal Substances 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 41
- 238000002347 injection Methods 0.000 claims description 40
- 239000007924 injection Substances 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 150000001340 alkali metals Chemical group 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 13
- 150000002910 rare earth metals Chemical class 0.000 claims description 13
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
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- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
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- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- RIUWBIIVUYSTCN-UHFFFAOYSA-N trilithium borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-] RIUWBIIVUYSTCN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
The present invention relates to a kind of organic electroluminescence devices, the organic electroluminescence device includes first electrode, at least one second electrode, at least one luminescent layer and at least one electron transporting zone, wherein the luminescent layer and the electron transporting zone are arranged between at least one described second electrode and the first electrode, and the electron transporting zone is arranged between the luminescent layer and at least one described second electrode, wherein at least one described electron transporting zone includes：First electron transfer layer, first electron transfer layer preferably do not include n-type dopant；And performance enhancing layer, the performance enhancing layer have≤1.6 refractive index at the wavelength of 1200nm；Wherein first electron transfer layer is arranged between the luminescent layer and the performance enhancing layer；And the performance enhancing layer is arranged between first electron transfer layer and at least one described second electrode.
Description
Technical field
The present invention relates to a kind of organic electroluminescence devices.
Background technique
The light extraction efficiency of OLED is only the 25% of the whole light generated in OLED device.By using known in the literature
Low-index material can get the improved light extraction efficiency of OLED device.It is known that needing the low-refraction of suitable high concentration
Material (50%) significantly reduces the effective refractive index of organic layer and significantly increases light extraction efficiency.
On the other hand, the low-index material of high concentration is introduced into the charge that may cause these layers in charge transport layer
The strong loss of transport property leads to the higher voltage of OLED device, the efficiency of reduction and final lower the operation is stable
Property.
Describe the use of low-index material in US 2007/114919, it was demonstrated that low-index material is in p-type doping
Hole transmission layer and luminescent layer in effect.Here, the improvement of efficiency increases along with the voltage of OLED device.Related device
The information of durability and service life does not provide in US 2007/114919.In addition, not sent out in US 2007/114919
Now it is applied to the example of electron transporting zone.
Silsesquioxane is described in WO 2002/1005971 as use of the low-index material in OLED.However,
In WO 2002/1005971 both the electron-transport without open low-index layer and also without openly low-index layer oxidation also
Original doping.Fluoro silsesquioxane is disclosed in WO 012/053414 in conjunction with laminate coat for solar battery, and fluorine
It is disclosed in WO 2016/017527 in conjunction with electrolyte or electrode assembly for solid state battery for silsesquioxane.
Summary of the invention
Therefore, the purpose of the present invention is to provide the organic electroluminescence devices for overcoming prior art disadvantage, especially mention
Avoid for the low-index material comprising high concentration but simultaneously disadvantage in charge transport quality, higher voltage, reduction effect
The organic electroluminescence device of rate and lower job stability and durability.
The purpose is realized by the inclusion of organic electroluminescence device below：At least one second electrode, first electrode,
At least one luminescent layer and at least one electron transporting zone, wherein the luminescent layer and the electron transporting zone are arranged in institute
It states between first electrode and at least one described second electrode, and the electron transporting zone is arranged in the luminescent layer and institute
It states between at least one second electrode, wherein at least one described electron transporting zone includes a) the first electron transfer layer, it is described
First electron transfer layer does not preferably include n-type dopant；And b) performance enhancing layer, wavelength of the performance enhancing layer in 1200nm
Locate the refractive index with≤1.6；Wherein first electron transfer layer be arranged in the luminescent layer and the performance enhancing layer it
Between；The performance enhancing layer is arranged between first electron transfer layer and at least one described second electrode.
In such as organic light emission two of the organic electroluminescence device with only one first electrode and only one second electrode
In the case where pole pipe, the first electrode can be anode, and the second electrode can be cathode.With more than two
In the case where the organic electroluminescence device of electrode such as organic electroluminescent transistor, the first electrode can be gate electrode
(coordination electrode), one in the second electrode can be source electrode (cell electrodes), and another in the second electrode
It is a to can be drain electrode (hole electrode).
In another embodiment, the organic electroluminescence device also includes at least one hole transporting zone.?
In one embodiment, the hole transporting zone is arranged between the first electrode and at least one described second electrode.
In another embodiment, the hole transporting zone is arranged between the first electrode and the luminescent layer.According to another
One embodiment, the luminescent layer are arranged between the hole transporting zone and the electron transporting zone.
In one embodiment, the electron transporting zone also includes electron injection middle layer, wherein the electronics is infused
Enter middle layer to be arranged between first electron transfer layer and the performance enhancing layer.
In another embodiment, the organic electroluminescence device is Organic Light Emitting Diode or organic electroluminescent
Transistor.
In another embodiment, the performance enhancing layer includes selected from silsesquioxane, alkane, perfluoro alkane, complete
Low refractive material in fluoroalkyl phosphonic acids, perfluor phosphine oxide and metal fluoride.
In another embodiment, silsesquioxane is by general formula SixRxO1.5xIt indicates, wherein R is alkyl, the alkyl
It may include that at least one is selected from the hetero atom of B, Si, N, P, O and S and/or may include at least one is the substituent group of halogen atom；
And x is selected from 6,8,10,12,14 and 16.
In one embodiment, the alkane is selected from the alkane with 18 to 60 carbon atoms.
In another embodiment, the metal fluoride is selected from or mixtures thereof LiF, NaF, KF.
In another embodiment, the low refractive material is selected from
Or mixtures thereof LiF.
In another embodiment, the performance enhancing layer also includes n-type dopant, wherein the n-type dopant is selected
From alkali metal, alkaline-earth metal, rare earth metal, alkali metal, alkaline-earth metal, the organic complex of rare earth metal or alkali metal, alkaline earth
Metal, the halide of rare earth metal or the n-type dopant are the compounds indicated by one of following formula：
Or mixtures thereof.
In another embodiment, the organic electroluminescence device successively includes first electrode, p-type doping hole biography
Defeated layer, the first optional hole transmission layer, the second optional hole transmission layer, the luminescent layer, first electron transfer layer,
The optional electron injection middle layer, the performance enhancing layer and at least one described second electrode, wherein the electronics is infused
Entering middle layer can be n-type doping electron transfer layer.
Detailed description of the invention
The definition of layer in Fig. 1-OLED.The sequence and quantity of layer in Fig. 1 are to an embodiment of the invention
Example.
Fig. 2-simulated experiment shows the efficiency of the optical coupling output from OLED with the drop of the refractive index of performance enhancing layer
It is low and increase.The analogy method is using " the light-emitting film optical simulator developed by Zurich University of Applied Sciences
(ETFOS) " the luminous model of the dipole with transfer matrix.The refractive index of performance enhancing layer changes between 1.30 and 1.85.
Arrangement of the oled layer laminated construction in table 3.OLED is the wherein first electrode and substrate of glass (refractive index n=1.5)
The bottom emission device directly contacted, optical coupling output occur across the substrate of glass.
Fig. 3-does not have performance in the case where LRIC and in the case where the LRIC with incrementss to increase in performance enhancing layer
The refractive index of strong layer.The maximum amount of LRIC leads to minimum refractive index, and such as by VASE, using spectroscopic ellipsometers, (Woolam is public
Department) measurement as.
Other than composition listed above (that is, layer and the material for being used to prepare layer), organic electroluminescent of the invention
Device may include other compositions, such as substrate, hole transporting zone, hole injection layer, p-type dopant, electron-transporting matrix
Compound, electron injecting layer etc..About the further details of feasible each embodiment, especially it is used to form of the invention
The suitably-arranged of the said modules of organic electroluminescence device will be explained in following part.Attached drawing will be referred in this respect
1, attached drawing 1 schematically shows the possible arrangement of organic electroluminescence device of the invention.However, those skilled in the art know
Know following fact：Embodiment shown in Fig. 1 only there is illustrative property and different arrangements be it is feasible, in difference
Arrangement in there are other composition or omit it is (nonessential) composition.
In Fig. 1, appended drawing reference indicates the different layers of organic electroluminescence device as follows：
001- substrate
100- first electrode
111- hole injection layer (HIL)
The first hole transmission layer of 112- (the first HTL)
The second hole transmission layer of 113- (the 2nd HTL)
120- luminescent layer (EML)
The first electron transfer layer of 131- (the first ETL)
132- electron injection middle layer (EIIL)
133- performance enhancing layer (PEL)
134- electron injecting layer (EIL)
At least one second electrode of 140-
150- hole transporting zone
The electron transporting zone 160-
Substrate
Substrate (001) can be any substrate for being commonly used to manufacture Organic Light Emitting Diode.If light is sent out across substrate
Out, then substrate can be with excellent mechanical strength, thermal stability, transparency, surface flatness, property easy to operate and waterproof
The transparent material of property, such as substrate of glass or transparent plastic substrate.If light is issued across top surface, substrate be can be
Bright or opaque material, such as substrate of glass, plastic-substrates, metallic substrates or silicon base.
First electrode
It can be used to form first electrode compound by depositing or sputtering and form first electrode (100).For shape
It can be high work function compound at the compound of first electrode, to promote hole to inject.First electrode is further selected from low evolution
Function material (that is, aluminium, silver), to promote electron injection.First electrode can be anode.First electrode can be transparent or reflection electricity
Pole.Electrically conducting transparent compound such as tin indium oxide (ITO), indium zinc oxide (IZO), stannic oxide (SnO2) and zinc oxide (ZnO) can
It is used to form first electrode 100.First electrode 100 also can be used magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca),
Magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), silver-colored (Ag), golden (Au) etc. are formed.
First electrode 100 can be formed by high-conductivity metal such as copper (Cu) or silver-colored (Ag).
Hole transporting zone
Hole transporting zone (150) may include that hole injection layer (111), the first hole transmission layer (112) and/or second are empty
Cave transport layer (113).
Hole injection layer (HIL)
It describes and is suitable for the invention in 2002/158242 A of US, 1988587 A1 of EP 1596445 A1 and EP
The hole injection layer (111) of organic electroluminescence device such as OLED.
Can by vacuum deposition, spin coating, printing, casting, slit coventry type die head coventry are extrusion coated, Langmuir-Blodgett is heavy
Product etc. forms HIL on the first electrode.
When forming HIL using vacuum deposition, sedimentary condition can be according to the compound and HIL for being used to form HIL
Desired structure and thermal property and change.However, may include 100 DEG C to 500 DEG C for vacuum-deposited condition in general
Depositing temperature, 10-8To 10-3Hold in the palm the pressure of (1 support is equal to 133.322Pa or 1.33322 millibar) and 0.1 to 10nm/ second sink
Product rate.
When forming HIL from solution using deposition, application conditions may include the painting of about 2000rpm to about 5000rpm
Cloth speed and about 80 DEG C to about 200 DEG C of heat treatment temperature.After being coated, heat treatment removes solvent.
HIL can be formed by any compound for being typically formed HIL.The example that can be used to form the compound of HIL
Including phthalocyanine compound such as copper phthalocyanine (CuPc), 4,4 ', 4 "-three (3- methylphenylphenyl amino) triphenylamines (m-MTDATA),
TDATA, 2T-NATA, polyaniline/dodecyl benzene sulfonic acid (Pani/DBSA), poly- (3,4- ethyldioxythiophene)/poly- (4- benzene
Vinyl sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA) and polyaniline/poly- (4- styrene sulfonate)
(PANI/PSS)。
HIL may include p-type dopant or be made of p-type dopant, and the p-type dopant can be selected from four fluoro- four cyanogen
Base quinone bismethane (F4TCNQ), 2,2 '-(two subunit of perfluor naphthalene -2,6-) two malononitrile or 2,2 ', 2 "-(cyclopropane -1,2,3- three
Subunit) three (2- (to cyano tetrafluoro phenyl) acetonitriles), but not limited to this.HIL can be passed selected from the hole doped with p-type dopant
Defeated matrix compounds.It is known doping hole mobile material representative instance be：Doped with four that lumo energy is about -5.2eV
The HOMO energy level of fluoro- four cyano quinone bismethane (F4TCNQ) is about copper phthalocyanine (CuPc), the phthalein doped with F4TCNQ of -5.2eV
Cyanines zinc (ZnPc) (HOMO=-5.2eV), α-NPD (N, N '-bis- (naphthalene -1- the base)-N, N '-bis- (phenyl)-doped with F4TCNQ
Benzidine), doped with the α-NPD of 2,2 '-(two subunit of perfluor naphthalene -2,6-) two malononitrile.P-type dopant concentration can be selected from 1
Weight % to 20 weight %, more preferable 3 weight % to 10 weight %.
The thickness of HIL can be in the range of from about 1nm to about 100nm, for example, from about 1nm to about 25nm.When HIL's
Thickness within this range when, HIL can have excellent hole-injection characteristics, the significant loss without having driving voltage.
In one embodiment, HIL includes hole mobile material and p-type dopant.
In another embodiment, HIL is made of p-type dopant.
P-type dopant
P-type dopant can be the change of quinone derivative, Radialene compounds, metal oxide, metal complex and cyano-containing
One of object is closed, but not limited to this.The non-limiting example of p-type dopant is quinone derivative such as four cyano quinone bismethane
(TCNQ), 2,3,5,6- tetra- fluoro- four cyano-Isosorbide-5-Nitraes-benzoquinones bismethane (F4-TCNQ), Radialene compounds such as PD-1 etc., metal oxygen
Compound such as tungsten oxide, molybdenum oxide etc., metal complex such as three [1,2- bis- (trifluoromethyl) ethane -1,2- dithiolenes] molybdenum (Mo
(tfd)3) etc. and cyano-containing for example following compound PD-2 of compound.
In another embodiment, p-type dopant can be as in WO 2017/029370 and WO 2017/029366
The neutral metal amide compound of description.
Hole transmission layer (HTL)
Hole transmission layer (being especially the first hole transmission layer and the second hole transmission layer) may include hole mobile material.
The compound that can be used is disclosed in such as Yasuhiko Shirota and Hiroshi Kageyama, Chem.Rev., and (chemistry is commented
By) in 2007,107,953-1010, be herein incorporated by reference.
In one embodiment, hole transmission layer may include p-type dopant.
First hole transmission layer (112) can by vacuum deposition, spin coating, slit coventry type die head coventry is extrusion coated, print, pour
Casting, Langmuir-Blodgett (LB) deposition etc. are formed on HIL.
In one embodiment, the first hole transmission layer can directly be contacted with HIL.
In one embodiment, the first hole transmission layer can directly be contacted with the second hole transmission layer.
In another embodiment, the first hole transmission layer can directly be contacted with luminescent layer.
In a preferred embodiment, the first hole transmission layer is free of p-type dopant.
Second hole transmission layer (113) can by vacuum deposition, spin coating, slit coventry type die head coventry is extrusion coated, print, pour
Casting, Langmuir-Blodgett (LB) deposition etc. are formed on the first hole transmission layer (113).
In one embodiment, the second hole transmission layer can directly be contacted with HIL.
In one embodiment, the second hole transmission layer can directly be contacted with the first hole transmission layer.
In another embodiment, the second hole transmission layer can directly be contacted with luminescent layer.
In a preferred embodiment, the second hole transmission layer is free of p-type dopant.
When forming corresponding hole transmission layer by vacuum deposition or spin coating, condition for depositing and being coated with can be with
The condition for being used to form hole injection layer is similar.However, according to the compound for being used to form respective hole transport layer, vacuum or molten
The condition of liquid deposition can change.
In one embodiment, the first hole transmission layer (112) and/or the second hole transmission layer (113) can serve as
Electronic barrier layer.The function of electronic barrier layer (EBL) is that electronics is prevented to be transferred to hole transmission layer from luminescent layer, thus by electronics
It is limited in luminescent layer.Efficiency, operating voltage and/or service life are improved as a result,.
The example that can be used to form the compound of HTL is：Carbazole derivates such as N- phenyl carbazole or polyvinyl carbazole；
Bis- (3- the aminomethyl phenyl)-N of benzidine derivative such as N, N ' -, N '-diphenyl-[1,1- biphenyl] -4,4 '-diamines (TPD) or N,
N '-two (naphthalene -1- base)-N, N '-diphenylbenzidine (α-NPD)；And triphenylamine compound, such as 4,4 ', 4 "-three (N- carbazoles
Base) triphenylamine (TCTA).Among these compounds, TCTA with transporting holes and can inhibit exciton diffusion into EML.
The thickness of HTL can be in following range：About 5nm to about 250nm, preferably from about 10nm are to about 200nm, further about
20nm to about 190nm, further about 40nm to about 180nm, further about 60nm to about 170nm, further about 80nm is to about
160nm, further about 100nm to about 160nm, further about 120nm to about 140nm.The preferred thickness of HTL can be 170nm
To 200nm.
When the thickness of HTL in the range when, HTL can have excellent hole transporting properties, without driving voltage
Significant loss.
The function of electronic barrier layer (EBL) is that electronics is prevented to be transferred to hole transmission layer from luminescent layer, and thus by electronics
It is restricted to luminescent layer.Efficiency, operating voltage and/or service life are improved as a result,.In general, electronic barrier layer includes triaryl amination
Close object.Triarylamine compound can have the lumo energy than hole transmission layer closer to the lumo energy of vacuum level.With
The HOMO energy level of hole transmission layer is compared, and electronic barrier layer can have the HOMO energy level further from vacuum level.Electronic barrier layer
Thickness can be selected between 2nm and 20nm.
If electronic barrier layer has high triplet level, triplet control layer can also be described as.
If the function of triplet control layer is to reduce the quenching of triplet using phosphorescence green or blue light-emitting layer.
Thus, it is possible to realize the higher luminous efficiency from phosphorescence luminescent layer.Triplet control layer is selected from triplet energy level and is higher than phase
The triarylamine compound of the triplet energy level of phosphorescent emitter in adjacent luminescent layer.Suitable triplet control layer, especially
Triarylamine compound is described in 2722908 A1 of EP, and is fully incorporated by reference.
Luminescent layer (EML)
Can by vacuum deposition, spin coating, slit coventry type die head coventry be extrusion coated, printing, casting, LB etc. is in the first hole transport
Luminescent layer (120) are formed on layer (112) or the second hole transmission layer (113).When forming EML using vacuum deposition or spin coating,
Condition for depositing and being coated with can be similar with the condition for being used to form HIL.
However, the condition of deposition and coating can change according to the compound for being used to form EML.
Luminescent layer (EML) can be formed by the combination of main body and illuminator dopant.In a preferred embodiment, it sends out
Photosphere is made of main body and illuminator dopant.
It can specify that luminescent layer does not include the compound of formula (I).
Luminescent layer (EML) can be formed by the combination of main body and illuminator dopant.The example of the main body is Alq3、4,
4 '-N, N '-two carbazole-biphenyl (CBP), poly- (n- vinyl carbazole) (PVK), 9,10- bis- (naphthalene -2- base) anthracene (ADN), 4,4 ',
4 "-three (carbazole -9- base)-triphenylamines (TCTA), 1,3,5- tri- (N- phenylbenzimidazol -2- base) benzene (TPBI), 3- tert-butyl -
Bis- -2- naphthyl anthracene (TBADN) of 9,10-, talan arlydene (DSA) and bis- (2- (2- hydroxy phenyl) benzothiazole) zinc (Zn
(BTZ)2)。
Illuminator dopant can be phosphorescent emitter or fluorescent illuminant.Phosphorescent emitter and postponed by thermal activation glimmering
The luminous illuminator of light (TADF) mechanism is preferred due to its higher efficiency.Illuminator can be small molecule or
Polymer.
The example of red emitter dopant is PtOEP, Ir (piq) 3 and Btp2Lr (acac), but not limited to this.These
Compound is phosphorescent emitter, it is also possible, however, to use fluorescent red illuminator dopant.
The example of phosphorescence green illuminator dopant is Ir (ppy)3(ppy=phenylpyridine), Ir (ppy)2(acac)、Ir
(mpyp)3。
The example of phosphorescence blue-light emitting body dopant is F2Irpic、(F2ppy)2Ir (tmd) and Ir (dfppz)3With three
Fluorenes.4,4 '-bis- (4- diphenylaminostyrene base) biphenyl (DPAVBi), 2,5,8,11- tetra-tert (TBPe) are fluorescence
The example of blue-light emitting body dopant.
Based on the main body of 100 parts by weight, the amount of dopant can be in the range of about 0.01 parts by weight to about 50 parts by weight.
Alternatively, luminescent layer may include light emitting polymer or be made of light emitting polymer.EML can have about 10nm to about
The thickness of 100nm, for example, about 20nm to about 60nm.When the thickness of EML within this range when, EML can have excellent light hair
It penetrates, and driving voltage does not dramatically increase.
In one preferred embodiment, comprising light emitting polymer or the luminescent layer and electronics that are made of light emitting polymer
Transmission region directly contacts.
In one preferred embodiment, the luminescent layer formed comprising light emitting polymer or by light emitting polymer and hole
Transmission region directly contacts.
Electron transporting zone
The electron transporting zone (160) of the laminated construction of layer in OLED can be set on luminescent layer (120).Electronics passes
Defeated region (160) includes the first electron transfer layer (131) and performance enhancing layer (133).In one embodiment, electron-transport
Region (160) can additionally comprise electron injection middle layer (132).
In a preferred embodiment, electron injection middle layer (132) can be direct with the first electron transfer layer (131)
It contacts and is directly contacted with performance enhancing layer (133).
In another embodiment, electron transporting zone (160) may include electron injecting layer (134).
In one embodiment, electron injecting layer (134) is directly contacted at least one described second electrode.
First electron transfer layer (the first ETL)
First electron transfer layer (131) can by using vacuum deposition, spin coating, slit coventry type die head coventry be extrusion coated, printing,
Casting, LB deposition etc. are formed on EML, to prevent hole to be diffused into ETL.First ETL can serve as hole blocking layer
(HBL).When EML includes phosphorescent dopants, HBL can also have triplet exciton barrier functionality, to prevent triplet exciton from expanding
It is scattered in electron transporting zone.
In a preferred embodiment, first electron transfer layer is free of n-type dopant.
First electron transfer layer can be used as the hole blocking layer in OLED of the invention, such as 2015/207093 A of US
With described in 2015/060794 A of US, it is fully incorporated herein by reference.
When forming the first electron transfer layer using vacuum deposition or spin coating, condition for depositing and being coated with can with
It is similar in the condition for forming HIL (111).However, depositing and being coated with according to the compound for being used to form the first electron transfer layer
Condition can change.Any compound for being typically formed the first electron transfer layer can be used.It is used to form the first electronics
The example of the compound of transport layer includesOxadiazole derivative, triazole derivative, pyrrolotriazine derivatives, acridine derivatives and phenanthrene are coughed up
Quinoline derivant.
In one embodiment, the compound for being used to form the first electron transfer layer is 1,3, the 5- triazine derivatives replaced
Object.
If the first electron transfer layer has high triplet energy level, triplet control layer can also be described as.
If the function of triplet control layer is to reduce the quenching of triplet using phosphorescence green or blue light-emitting layer.Thus, it is possible to
Realize the higher luminous efficiency from phosphorescence luminescent layer.Triplet control layer is higher than in adjacent emissive layers selected from triplet energy level
Phosphorescent emitter triplet energy level heteroaryl compound.
In one embodiment, the first electron transfer layer may be formed on luminescent layer.
In a preferred embodiment, the first electron transfer layer can directly be contacted with luminescent layer.
First electron transfer layer can have about 5nm to about 100nm, the thickness of for example, about 10nm to about 30nm.When the first electricity
The thickness of sub- transport layer in the range when, the first electron transfer layer can have an excellent hole blocking properties, and driving voltage
Do not dramatically increase.
In one embodiment, the first ETL contains the biography of the electronics comprising two or more individual electron transfer layers
Defeated layer stacked structure.
N-type dopant
N-type dopant is understood to such compound, if embedded it in electron transfer layer or electron injecting layer,
The concentration of free electron is then increased compared to pure matrix under identical physical condition, so that including the n-type dopant
The electric conductivity of layer is higher than the electric conductivity of pure hypothallus.
Under the operating condition of electroluminescent device such as OLED, n-type dopant does not shine.In one embodiment, n
Type dopant is selected from electroneutral metal complex and/or electroneutral organic group.
The most practical benchmark of n-type dopant intensity is the value of its oxidation-reduction potential.It can be more with regard to oxidation reduction potential value
For negative, it is not particularly limited.
If relative to ferrocene/ferroceneReference redox electricity is measured by cyclic voltammetry, for organic
The oxidation-reduction potential of common electron-transporting matrix in light emitting diode is substantially in the range of about -1.8V to about -3.1V；It can
Effectively the reality of the oxidation-reduction potential of the n-type dopant of this matrix of n-type doping can application range be in from about -1.7V to
In the slightly wider range of about -3.3V.
What the measurement of oxidation-reduction potential was actually for being made of the reduction form and oxidised form of the same compound
Corresponding oxidation reduction electricity is to progress.
In the case where n-type dopant is electroneutral metal complex and/or electroneutral organic group, redox electricity
The measurement of position is actually for by oxidation-reduction pair progress formed below：
(i) electroneutral metal complex and its shape and capturing an electronics from the electroneutral metal complex
At cation group, or
(ii) electroneutral organic group and it formed and capturing an electronics from the electroneutral organic group
Cation.
Preferably, if relative to ferrocene/ferroceneOxidation-reduction pair is by cyclic voltammetry for by following
The corresponding oxidation reduction electricity of composition is to measuring, then the oxidation of electroneutral metal complex and/or electroneutral organic group is also
Former current potential can have that ratio -1.7V is more negative, preferably ratio -1.9V is more negative, more preferable ratio -2.1V is more negative, even more preferably from more than -2.3V
Negative, the most preferably more negative value of ratio -2.5V,
(i) electroneutral metal complex and its shape and capturing an electronics from the electroneutral metal complex
At cation group, or
(ii) electroneutral organic group and it formed and capturing an electronics from the electroneutral organic group
Cation.
In one preferred embodiment, the oxidation-reduction potential of n-type dopant is between following two value：Than selected
The value, more negative than the value of the reduction potential of selected electron-transporting matrix of the value corrigendum about 0.5V of the reduction potential of electron-transporting matrix
The value of about 0.5V.
The electroneutral metal complex for being suitable as n-type dopant can be some transition metal for example in low-oxidation-state
Strong reducing property complex compound.In one embodiment, n-type dopant can be selected from the guanidine of Cr (II), Mo (II) and/or W (II)
Base complex such as W2(hpp)4, as in WO2005/086251 in greater detail.
Be suitable as n-type dopant electroneutral organic group can be it is for example steady from it by providing additional energy
The organic group generated in fixed dimer, oligomer or polymer, such as in EP 1837926B1,2007/107306 WO or WO
In 2007/107356 in greater detail.The specific example of these proper groups can be oxadiazolyl group,Oxazolyl group
And/or thiazolyl group.
Metal element is suitable as n-type dopant.Metal element is understood in pure metallic state, metal alloy state
Or the metal in free atom or metal cluster state.It is appreciated that by vacuum thermal evaporation from metal phase for example from pure bulk
The metal of metal deposit is with the evaporation of its element form.It is also to be understood that if the metal element of evaporation deposits together with covalent matrix,
Then metallic atom and/or cluster are embedded in covalent matrix.In other words, it is understood that any metal prepared by vacuum thermal evaporation
The covalent material of doping contains the metal at least partly in its element form.
For the use in consumption electronic product, the only core very long containing stable nuclide or radioactive decay half-life period
The metal of element is applicable.It is horizontal as acceptable nuclear stability, the nuclear stability of natural potassium can be taken.
In one embodiment, the n-type dopant is selected from electropositive metal, and the electropositive metal is selected from alkali gold
Belong to, alkaline-earth metal, rare earth metal and First Transition period metal Ti, V, Cr and Mn.Preferably, n-type dopant be selected from Li, Na,
K,Rb,Cs,Mg,Ca,Sr,Ba,Sm,Eu,Tm,Yb；It is more preferably selected from Li, Na, K, Rb, Cs, Mg, Ca and Yb, even more preferably from choosing
From Li, Mg, Ca and Yb.
The n-type dopant can not shine substantially.
Electron-transporting matrix compound
Device according to the present invention for example comprising hole blocking layer, electron injecting layer device in electron transporting zone
Various embodiments may include electron-transporting matrix compound.
Electron-transporting matrix is not particularly limited.With include other materials class in device of the present invention outside luminescent layer
Seemingly, electron-transporting matrix can not shine.
According to one embodiment, electron-transporting matrix can be organic compound, organo-metallic compound or metal network
Close object.
According to one embodiment, electron-transporting matrix can be being total to for the conjugated system comprising at least six delocalized electron
Valence compound.Covalent material in broadest feasible meaning can be understood as a kind of such material, wherein all chemical bonds
At least 50% be covalent bond, wherein coordinate bond is also considered as covalent bond.In this application, the term is in broadest meaning
On cover all common electron-transporting matrix, be mainly selected from organic compound, be also selected from for example comprising structure division (institute
Structure division is stated not comprising carbon) compound, such as substituted 2,4,6- tri- boron are miscellaneous -1,3,5-triazines, or are selected from metal network
Close object such as three (8-hydroxyquinoline) aluminium.
Molecule covalent material may include low molecular weight compound, it is preferable that it can be sufficiently stable can pass through Vacuum Heat
Evaporate (VTE) processing.Alternatively, covalently material may include the covalent compound of polymerization, being preferably soluble in solvent simultaneously therefore can be molten
The compound of liquid form processing.It is appreciated that the substantially covalent material of polymerization can be crosslinked to form infinitely irregular netted
Object, however, the substantially covalent matrix compounds for assert the polymerization of this crosslinking still include skeleton and peripheral atoms.Covalently
The skeletal atom of compound and at least two adjacent atom covalent bonds.Other atoms of covalent compound are and individually adjacent to former
The covalently bound peripheral atoms of son.Inorganic crystals of infinite or complete friendship with some covalent key but substantially free of peripheral atoms
The mesh of connection, such as silicon, germanium, GaAs, indium phosphide, zinc sulphide, silicate glass are not considered in the sense that the application
It is covalent matrix, because covalent material fully crosslinked in this way is only former comprising periphery on the surface of the phase formed by this material
Son.If at least cation or at least anion include at least ten covalently bound atoms, comprising cation and anion
Compound be still considered as it is covalent.
The preferred embodiment of shared eletron transmission matrix compounds is organic to be mainly made of covalently bound C, H, O, N, S
Compound optionally also includes covalently bound B, P, As, Se.In one embodiment, electron-transporting matrix chemical combination
Object lacks metallic atom, and its most of skeletal atom is selected from C, O, S, N.
In another embodiment, electron-transporting matrix compound include at least six, more preferably at least ten, also more
The conjugated system of preferably at least 14 delocalized electrons.
The example of the conjugated system of delocalized electron is the system of alternate pi bond and σ key.Optionally, have between its atom
Having the two atomic structure unit of one or more of pi bond can be replaced by the atom at least one lone electron pair, usually selected
It replaces from the bivalent of O, S, Se, Te or is replaced by the triad selected from N, P, As, Sb, Bi.Preferably, delocalized electron
Conjugated system includes that at least one follows the aromatics or heteroaromatic rings of huckel rule.It is further preferred that electron-transporting matrix chemical combination
Object may include at least two aromatics or heteroaromatic rings by being covalently keyed or condensing.
In one embodiment, electron-transporting matrix compound include by the covalently bound molecular ring of original, and
At least one atom is phosphorus in the ring.
It in a preferred embodiment, is phospha English in heptan ring by the molecular phosphorous ring of covalently bound original.
In another preferred embodiment, electron-transporting matrix compound includes phosphine oxide group.
In another preferred embodiment, electron-transporting matrix compound includes oxadiazole.
It is further preferred that the substantially covalent matrix compounds may include the heterocycle containing at least one nitrogen-atoms.It is special
Example not advantageous as the nitrogen-containing heterocycle compound of the electron-transporting matrix compound for device of the present invention is individually
It or in a joint manner include matrix below：Pyridine structure part, diazine structure part, triazine structure part, quinoline structure portion
Divide, benzoquinoline structure division, quinazoline structure part, acridine structure division, benzacridine structure division, dibenzo acridine knot
Structure part, diazole structure division and benzodiazole structure division.
The electronics matrix compounds can have >=400g/mol to≤850g/mol, preferably >=450g/mol to≤
The molecular weight (Mw) of 830g/mol.If selecting molecular weight within this range, good long-time stability can be being observed
At a temperature of realize extremely reproducible evaporation and deposition in a vacuum.
Preferably, the matrix compounds can not shine substantially.
Electron injection middle layer (EIIL)
Condition when vacuum deposition can be used in electron injection middle layer (132) or spin coating is formed, for depositing and being coated with
It can be similar with the condition for being used to form HIL (111).However, according to the compound for being used to form performance enhancing layer, deposition and painting
The condition of cloth can change.
Electron injection middle layer may include at least one electron-transporting matrix compound and at least one n-type dopant.
In one embodiment, electron-transporting matrix compound includes at least one oxadiazole.
In a preferred embodiment, electron-transporting matrix compound includes at least one phosphine oxide group.
In one embodiment, n-type dopant can be selected from alkali metal, alkaline-earth metal, rare earth metal, alkali metal, alkali
Earth metal, the organic complex of rare earth metal or electroneutral transition metal complex.
In one embodiment, n-type dopant is selected from electropositive metal, and the electropositive metal is selected from alkali metal, alkali
Earth metal, rare earth metal and First Transition period metal Ti, V, Cr and Mn.Preferably, n-type dopant be selected from Li, Na, K, Rb,
Cs,Mg,Ca,Sr,Ba,Sm,Eu,Tm,Yb；Be more preferably selected from Li, Na, K, Rb, Cs, Mg, Ca and Yb, even more preferably from selected from Li,
Mg, Ca and Yb.
In one embodiment, the concentration of the electropositive metal in the electron-transporting matrix compound is in about 0.5 weight
In the range of measuring % to about 25 weight %, preferably in the range of about 1 weight % to about 20 weight %, more preferably in about 2 weights
In the range of measuring % to about 15 weight %, most preferably in the range of about 3 weight % to about 10 weight %.
In another embodiment, n-type dopant can be selected from the complex compound of the transition metal of low-oxidation-state, such as Cr
(II), the guanidine radicals complex compound of Mo (II) and/or W (II).
In another embodiment, n-type dopant be selected from the compound indicated by one of following formula or by following formula it
One compound indicated：
Or mixtures thereof.
In one embodiment, the thickness of EIIL (132) is greater than about 0.1nm and lower than 50nm, preferably greater than 0.5nm and
Less than 30nm, also more preferably more than 1nm and less than 25nm.
In one embodiment, EIIL (132) is arranged in the first electron transfer layer (131) and performance enhancing layer (133)
Between.
In another embodiment, EIIL (132) is arranged as directly contacting with the first electron transfer layer (131).
In another embodiment, EIIL (132) is arranged as directly contacting with performance enhancing layer (133).
Performance enhancing layer (PEL)
Performance enhancing layer can be at wavelength 1200nm by ellipsometry measure refractive index be about≤1.6 appoint
What layer.
When using vacuum deposition or spin coating forming properties enhancement layer (133), condition for depositing and being coated with can be with
The condition for being used to form HIL (111) is similar.However, according to the compound for being used to form performance enhancing layer, the item of deposition and coating
Part can change.
In one embodiment, performance enhancing layer may include at least one electron-transporting matrix compound and at least one
Kind low-refraction compound (LRIC).
In the preferred embodiment, performance enhancing layer may include at least one electron-transporting matrix compound, at least one
Kind LRIC and at least one n-type dopant.
In one embodiment, electron-transporting matrix compound includes at least one oxadiazole.
In a preferred embodiment, electron-transporting matrix compound includes at least one phosphine oxide group.
In one embodiment, n-type dopant can be selected from alkali metal, alkaline-earth metal, rare earth metal, alkali metal, alkali
Earth metal, the organic complex of rare earth metal or electroneutral transition metal complex.
In one embodiment, n-type dopant is selected from electropositive metal, and the electropositive metal is selected from alkali metal, alkali
Earth metal, rare earth metal and First Transition period metal Ti, V, Cr and Mn.Preferably, n-type dopant be selected from Li, Na, K, Rb,
Cs,Mg,Ca,Sr,Ba,Sm,Eu,Tm,Yb；Be more preferably selected from Li, Na, K, Rb, Cs, Mg, Ca and Yb, even more preferably from selected from Li,
Mg, Ca and Yb.
In another embodiment, n-type dopant can be selected from the complex compound of the transition metal of low-oxidation-state, such as Cr
(II), the guanidine radicals complex compound of Mo (II) and/or W (II).
In another embodiment, n-type dopant be selected from the compound indicated by one of following formula or by following formula it
One compound indicated：
Or mixtures thereof.
When being measured under the wavelength of 1200nm by ellipsometry, performance enhancing layer can have 1.6 or smaller folding
Penetrate rate.
In one preferred embodiment, when being measured under the wavelength of 1200nm by ellipsometry, performance increases
The refractive index of strong layer is 1.6 or smaller and is greater than 1.0.
In preferred embodiment, when being measured under the wavelength of 1200nm by ellipsometry, performance enhancement
The refractive index of layer is 1.58 or smaller and is greater than 1.05.
In further preferred embodiment, when being measured under the wavelength of 1200nm by ellipsometry, performance
The refractive index of enhancement layer is 1.55 or smaller and is greater than 1.05.
In one embodiment, performance enhancing layer is arranged between first electrode and at least one described second electrode.
In one embodiment, performance enhancing layer is arranged in the first electron transfer layer and at least one described second electrode
Between.
In another embodiment, performance enhancing layer is arranged as directly contacting with the first electron transfer layer (131).
In one embodiment, performance enhancing layer is arranged as directly contacting with electron injection middle layer (132).
In another embodiment, performance enhancing layer is arranged as directly contacting with electron injecting layer (134).
In another embodiment, performance enhancing layer is arranged as directly contacting at least one described second electrode.
In one embodiment, the content of the LRIC in performance enhancing layer is greater than 5 mass % and less than 95 mass %.
In another embodiment, the content of LRIC is greater than 10 mass % and less than 90 mass % in performance enhancing layer.
In another embodiment, the content of LRIC is greater than 20 mass % and less than 80 mass % in performance enhancing layer.
In one embodiment, the content of n-type dopant is greater than 0.1 mass % and less than 30 matter in performance enhancing layer
Measure %.
In another embodiment, the content of n-type dopant is greater than 1 mass % and less than 20 matter in performance enhancing layer
Measure %.
In another embodiment, the content of n-type dopant is greater than 2 mass % and less than 15 matter in performance enhancing layer
Measure %.
In one embodiment, the thickness of performance enhancing layer (133) is greater than about 0.1nm and is less than 150nm, preferably greater than
1nm and be less than 100nm, also more preferably more than 10nm and be less than 100nm.
Low-refraction compound (LRIC)
Low-refraction compound according to the present invention can be inorganic material or organic material.
The example that can be used for the inorganic material of LRIC includes metal oxide, metal fluoride, Si oxide and metal
Oxide-Si oxide mixture.Metal fluoride is preferred embodiment.
Inorganic LRIC can be selected from AIF3、MgF2、Na3AIF6、CaF2、BaF2、SrF2、LiF、NaF、KF、CsF、Na20、
Li20、SiO2And SiO2/Na20Mixture.
In one preferred embodiment, inorganic LRIC is selected from AIF3、Na3AIF6、MgF2、CaF2、BaF2、SrF2、
LiF, NaF, KF and CsF.
The example that can be used for the organic material of LRIC includes fluorinated organic compound, alkyl compound, naphthenic base chemical combination
Object, cyclodextrin, cyclic ethers, catenne and Cucurbituril.
In one embodiment, LRIC is fluorinated organic compound.
Fluorine-containing organic LRIC can be selected from all-fluoroalkyl compound, perfluoroalkyl ether compound etc..
In one embodiment, organic LRIC is all-fluoroalkyl compound.
In another embodiment, organic LRIC is selected from perfluor dodecane, perfluor -2,7- dimethyl octane, perfluor -2,
11- dimethyl dodecyl and difluoro methyl ether/tetrafluoro ether copolymer.
In the present invention, inorganic LRIC can be mixed with organic LRIC.Mixed proportion is not particularly limited, can be can
It is formed in the range of good mixture and is arbitrarily selected.However, in this respect, the refractive index of LRIC mixture depends in mixture
The quality ratio of each LRIC.Therefore the content height in mixture compared with the LRIC of low-refraction is advantageous.
In one embodiment, when by ellipsometry measured under the wavelength of 1200nm when, LRIC have 1.5 or
Smaller refractive index.
In one preferred embodiment, when being measured under the wavelength of 1200nm by ellipsometry, LRIC tool
There are 1.4 or smaller refractive index.
In preferred embodiment, when being measured under the wavelength of 1200nm by ellipsometry, LRIC has
1.3 or smaller refractive index.
In one embodiment, LRIC is selected from silsesquioxane.
In another embodiment, LRIC is by general formula SixRxO1.5xThe compound of expression, wherein
R is alkyl, and the alkyl may include the hetero atom that at least one is selected from B, Si, N, P, O and S,
The alkyl includes at least one aromatics or heteroaromatic moiety, and the aromatics or heteroaromatic moiety are taken by least one
Dai Ji partially or even wholly replaces, wherein at least one described substituent group is selected from halogen and CN；
X is selected from 6,8,10,12,14 and 16；And
In another preferred embodiment, LRIC is the compound indicated by leading to formula (I)
Wherein
R1For the carbocyclic ring with 2 to 20 carbon atoms and comprising at least one fluoro or perfluoro or the group of carbon heterocyclic,
Wherein the carbocyclic ring of the fluoro or carbon heterocyclic can be unsubstituted or replaced by least one substituent group selected from the following：Alkane
Base, fluoro-alkyl and perfluoroalkyl；Wherein referred to that the carbon atom number for making 2 to 20 covers all carbon atoms, including is replaced
The carbon atom of base.
Wherein group R1It also may include the hetero atom that at least one is selected from B, Si, N, P, O and S；And
L is independently selected from (CH2) n and/or (CF2) m and/or (CzHxFy)
Wherein,
N and m is >=0 integer value
X=2z-y and x are >=1 integers
Y=2z-x and y are >=1 integers
Z is >=1 integer value
In another embodiment, LRIC be selected from alkane or perfluoro alkane, wherein carbon atom number be 18 to 60, preferably 25 to
55, more preferable 30 to 50.
In another embodiment, LRIC is selected from phosphorous compound, such as perfluoroalkyl phosphonic acids such as 1H, 1H, 2H,
2H- perfluorooctane phosphonic acids, perfluor phosphine oxide such as three (perfluorododecyl) phosphine oxide.
In another embodiment, LRIC be selected from ADD-1, ADD-2, ADD-3, ADD-4 or ADD-5 (being shown in Table 1) or its
Mixture.
Electron injecting layer (EIL)
Organic Light Emitting Diode may include electron injecting layer (134).
Optional EIL can promote injection of the electronics into electron transporting zone.
Electron injecting layer can be made of at least one metallic compound.
Metallic compound can be selected from metal halide, metallo-organic complex and/or zero-valent metal.
Preferably, metallic compound is selected from metal halide, metallo-organic complex and/or zero-valent metal, preferably alkali gold
Belong to halide, alkali metal organic complex, more preferable alkali halide, alkali metal organic complex, most preferably lithium fluoride and
Quinoline lithium (LiQ).
Metal halide can be with halide selected from the following：Wherein the metal is selected from Li, Na, K, Cs, Mg, Ca and Ba；
And halide is selected from F, Cl, Br and I, and preferably lithium halide.
Lithium halide can be selected from LiF, LiCl, LiBr or LiI, and preferred LiF.
The metallo-organic complex can be selected from metal quinolate, metal borate, metal phenates and/or metal Schiff
Alkali.
Preferably, metallo-organic complex can be lithium organic complex.
Preferably, lithium organic complex can be selected from quinoline lithium, lithium borate, the phenates of lithium and/or lithium schiff bases, preferably
Quinoline lithium complex with Formulas I, II or III：
Wherein,
-A1To A6It is identical or independently selected from CH, CR, N, O,
- R is identical or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl with 1 to 20 carbon atom, and
More preferable 8-hydroxyquinoline lithium.
The zero-valent metal can be selected from alkali metal, alkaline-earth metal, rare earth metal and/or the 3rd group 4 transition metal, preferably
Zero-valent metal be selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Yb, Sm, Eu, Nd, Tb, Gd, Ce, La, Sc and Y, more preferable zero
Valence metal is selected from Li, Na, Mg, Ca, Ba, Yb, and is selected from Li, Mg, Ba, Yb even more preferably from zero-valent metal.
Preferably, electron injecting layer is free of electron-transporting matrix compound.Therefore, electron injecting layer is not electron-transport
Layer.
In one embodiment, electron injecting layer is arranged between performance enhancing layer and cathode.
In a preferred embodiment, electron injecting layer is arranged as directly contacting with cathode.
In another embodiment, electron injecting layer is arranged as directly contacting with performance enhancing layer.
Be used to form EIL deposition and application conditions be used to form the deposition and application conditions of hole injection layer (HIL)
It is similar, however can be changed according to the material for being used to form EIL, deposition and application conditions.
The thickness of EIL can be in the range of about 1nm to 10nm.According to preferred embodiment, the thickness of electron injecting layer
Degree can be about >=1nm and about≤10nm, preferably from about >=2nm to about≤6nm, preferably from about >=3nm to about≤5nm, and more excellent
Select about >=3nm to about≤4nm.When the thickness of EIL within this range when, EIL according to the present invention can have improvement electronics infuse
Enter the significant decrease of performance, especially operating voltage and/or the increase of external quantum efficiency EQE.
Preferably, if performance enhancing layer (133) does not contain n-type dopant, there are electron injecting layers.
If performance enhancing layer (133) contains n-type dopant really, electron injecting layer (134) may not be present.
At least one second electrode
At least one described second electrode, preferably cathode, are formed on EIL.At least one described second electrode can be
Electron injection electrode.At least one described second electrode can be formed by or mixtures thereof metal, alloy, conductive compound.Institute
Low work function can be had by stating at least one second electrode.For example, at least one described second electrode can be by lithium (Li), magnesium
(Mg), aluminium (Al), aluminium (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver-colored (Ag) etc.
It is formed.In addition, at least one described second electrode can be formed by the transparent conductive material of such as ITO or IZO.Described at least one
A second electrode can be transparent or reflecting electrode.
The thickness of at least one second electrode can in the range of about 5nm to 1000nm, such as 10nm extremely
In the range of 100nm.When at least one described second electrode is in the range of 5nm to 50nm, even if using metal or metal
Alloy, electrode also will be transparent.
At least one described second electrode is not electron injecting layer or electron transfer layer.
In a preferred embodiment, at least one described second electrode is directly contacted with electron transporting zone (160).
It has surprisingly been found that when electron transporting zone (160) include non-luminescent body dopant when, may be implemented from it is described at least one
Very good electron injection of the second electrode to electron transporting zone (160).
When at least one described second electrode and electron injecting layer (134) directly contact, low-down work may be implemented
Make voltage and high external quantum efficiency EQE.The battery life of moving device increases as a result,.However, at least one described second electricity
Pole and electron injecting layer are if it exists, then they are different in component.
Light emitting diode (OLED)
According to an aspect of the invention, there is provided a kind of Organic Light Emitting Diode (OLED), it includes：Substrate, anode,
Hole injection layer, the first hole transmission layer, the second optional hole transmission layer, luminescent layer, the first electron transfer layer, optional electricity
Son injection middle layer, performance enhancing layer, optional electron injecting layer and cathode layer, wherein the layer is arranged according to the sequence.
According to another aspect of the present invention, a kind of Organic Light Emitting Diode (OLED) is provided, it includes：Substrate, anode,
Hole injection layer, the first hole transmission layer, the second optional hole transmission layer, luminescent layer, the first electron transfer layer, optional electricity
Son injection middle layer, performance enhancing layer, optional electron injecting layer, N-shaped charge generation layer, optional middle layer, p-type charge produce
Generating layer, third hole transmission layer, the 4th optional hole transmission layer, luminescent layer, the second electron transfer layer, optional electron injection
Middle layer, performance enhancing layer, optional electron injecting layer and cathode layer, wherein the layer is arranged according to the sequence.
The various embodiments of OLED according to the present invention, OLED can not include electron injecting layer.
The various embodiments of OLED according to the present invention, OLED can not include electron injection middle layer.
The various embodiments of OLED according to the present invention, OLED can not include electronic barrier layer.
The various embodiments of OLED according to the present invention, OLED can not include hole blocking layer.
The various embodiments of OLED according to the present invention, OLED can not include charge generation layer.
The various embodiments of OLED according to the present invention, OLED can not include the second luminescent layer.
The charge generation layer (CGL) that can be adapted for OLED of the invention describes in 2012/098012 A of US.
Charge generation layer is usually made of bilayer.Charge generation layer can be connection N-shaped charge generation layer and p-type charge produces
The pn-junction charge generation layer of generating layer.Pn-junction charge generation layer generates charge or is separated into hole and electronics；And by charge
It is injected into individual luminescent layer.In other words, N-shaped charge generation layer provides electricity for first luminescent layer adjacent with first electrode
Son, and p-type charge generation layer provides hole to second luminescent layer adjacent at least one described second electrode, it is possible thereby into
One step improves the luminous efficiency of the organic luminescent device comprising multiple luminescent layers, and at the same time driving voltage can be reduced.
P-type charge generation layer can by doped with p-type dopant metal or organic material constitute.Here, the metal
It can be selected from one of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni and Ti or be made of two or more
Alloy.Moreover, conventional material can be used in p-type dopant and the main body for the organic material doped with p-type dopant.Example
Such as, the p-type dopant can be selected from four fluoro- 7,7,8,8- four cyano quinone bismethanes (F4-TCNQ), four cyano quinone bismethane
Derivative, axis ene derivative, iodine, FeCl3、FeF3And SbC15One of.Equally, the main body can be selected from N, N '-
Two (naphthalene -1- base)-N, N- diphenyl-benzidine (NPB), N, bis- (3- the aminomethyl phenyl) -1,1- biphenyl-of N '-diphenyl-N, N ' -
One of 4,4 '-diamines (TPD) and N, N ', the N naphthalene of '-four benzidine (TNB).
N-shaped charge generation layer can by doped with n-type dopant metal or organic material constitute.The metal can be
Selected from one of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy and Yb.Equally, n-type dopant and
Main body for the organic material doped with n-type dopant can use conventional material.For example, n-type dopant can be alkali gold
Category, alkali metal compound, alkaline-earth metal or alkaline earth metal compound.More specifically, n-type dopant can be selected from Cs, K, Rb,
One of Mg, Na, Ca, Sr, Eu and Yb.The material of main part can be selected from three (8-hydroxyquinoline) aluminium, triazine, hydroxyl quinoline
One of quinoline derivant, indole derivatives and thiophene cough up derivative.
In another preferred embodiment, N-shaped charge generation layer is adjacently positioned with electron transfer layer.
In another preferred embodiment, p-type charge generation layer is adjacently positioned with hole transmission layer.
In one embodiment, organic electroluminescence device of the invention also may include containing Radialene compounds and/or
The layer of quinone diformazan hydride compounds.
In one embodiment, the Radialene compounds and/or the quinone diformazan hydride compounds can be one or more
Halogen atom and/or one or more electron-withdrawing groups replace.Electron-withdrawing group can be selected from itrile group, halogenated alkyl, or be selected from
Whole haloalkyl, or it is selected from perfluoroalkyl.Other examples of electron-withdrawing group can be acyl group, sulfonyl or phosphoryl.
Alternatively, acyl group, sulfonyl and/or phosphoryl may include halogenated and/or perhalogeno alkyl.In an embodiment
In, perhalogeno alkyl can be perfluoro hydrocarbyl.The example of perfluoro hydrocarbyl can be perfluoro-methyl, perfluoro-ethyl, perfluor third
Base, perfluoroisopropyl, perfluoro butyl, perfluorophenyl, perfluorotoluene base；The example of sulfonyl comprising halohydrocarbyl can be three
Methyl fluoride sulfonyl, pentafluoroethyl group sulfonyl, pentafluorophenyl group sulfonyl, heptafluoropropyl sulfonyl, nona-fluoro butyl group sulfonyl etc..
In one embodiment, the axis alkene and/or quinone diformazan hydride compounds may be embodied in hole injection layer, hole
In transport layer and/or hole generating layer, and the latter has the function of generating hole in charge generation layer or pn-junction.
In one embodiment, the Radialene compounds can have formula (XX) structure and/or the quinone diformazan alkanisation
Formula (XXIa) or the structure of (XXIb) can be had by closing object：
Wherein R1、R2、R3、R4、R5、R6、R7、R8、R11、R12、R15、R16、R20、R21Independently selected from above-mentioned electron-withdrawing group,
And R9、R10、R13、R14、R17、R18、R19、R22、R23And R24Independently selected from H, halogen and above-mentioned electron-withdrawing group.
Manufacturing method
According to various embodiments of the present invention, it can provide and a kind of be used to prepare organic electroluminescence device of the invention
Method, the method includes first electrode is formed on the substrate, and be sequentially depositing following other layers：Hole injection layer,
One hole transmission layer, optional second layer hole transmission layer, luminescent layer, the first electron transfer layer, among optional electron injection
Layer, performance enhancing layer, optional electron injecting layer and at least one the second electrode lay；Or these layers from it is described at least one
Two electrode layers start to deposit in a reverse direction.
According to various embodiments of the present invention, this method, which may also include, is formed on the substrate first electrode, hole injection
Layer, the first hole transmission layer, the second optional hole transmission layer, luminescent layer, the first electron transfer layer, in optional electron injection
Interbed, performance enhancing layer, optional electron injecting layer, N-shaped charge generation layer, optional middle layer, p-type charge generation layer,
Three hole transmission layers, the 4th optional hole transmission layer, luminescent layer, the second electron transfer layer, optional electron injection middle layer,
Performance enhancing layer, optional electron injecting layer and at least one the second electrode lay, wherein these layers are arranged according to the sequence；Or
These layers deposit in a reverse direction since at least one described the second electrode lay.
First electrode and/or at least one described second electrode can be deposited in substrate.Preferably, first electrode deposits
In substrate.
According to another aspect of the present invention, a kind of method for manufacturing Organic Light Emitting Diode (OLED), the side are provided
Method uses：
At least one sedimentary origin, preferably two sedimentary origins, and more preferably at least three sedimentary origins；And/or
It is deposited by vacuum thermal evaporation；And/or
It is handled and is deposited by solution, it is preferable that the processing is selected from spin coating, printing, casting and/or slit mould
It is extrusion coated.
Electronic device
On the other hand it is related to the electronic device comprising at least one Organic Light Emitting Diode (OLED).Include organic light emission two
The device of pole pipe (OLED) is, for example, display or illumination panel.
On the other hand it is related to the electronic device comprising at least one organic light-emitting transistor (OLET).Include organic light emission crystalline substance
The device of body pipe (OLET) is, for example, display or illumination panel.
Other aspects and/or advantage of the invention will be illustrated partially in the following description, and part will be from description
It is clear that can be to understand by the practice of the present invention.
In one embodiment, the electronic device is electroluminescent device.Preferably, electroluminescent device is organic
Light emitting diode.
In another embodiment, electroluminescent device is organic light-emitting transistor.
According to another aspect of the present invention, a kind of electronic device is provided, the electronic device includes at least one basis
Through the electroluminescent device of any embodiment described herein, it is preferable that the electronic device includes to run through the application
Organic Light Emitting Diode in one of embodiment of description.It is highly preferred that the electronic device is display device.
Details and definition of the invention
Term " alkyl " used herein refers to any list derived from any kind of saturation, insatiable hunger and/or aromatic hydrocarbon
Valence group.
Term " alkane " used herein refers to saturated hydrocarbons.It can be linear, branch or cricoid, and institute
Stating hydrogen atom can partly or entirely be replaced by other non-metallic atoms such as halogen, oxygen, nitrogen, sulphur, but not limited to this.
Term " fluoro " used herein refers at least one of hydrogen atom for including in wherein alkyl by fluorine original
The alkyl that son replaces.The fluoro group that wherein all hydrogen atoms are replaced by fluorine atoms is referred to as perfluor groups, and especially logical
Term " perfluoro " is crossed to indicate.
For the present invention, if including that a hydrogen atom in group is replaced by another group, the group quilt
Another group " substitution ", wherein another described group is substituent group.
For the present invention, statement about a layer between two other layers " between " be not excluded for other layers and deposit
Other layers may be arranged between a layer in one layer and described two other layers.For the present invention, it closes
Mean no longer to arrange other layers between the two layers in the statement " directly contact " that two layers are in direct contact with one another.It is deposited on
One layer at another layer of top is considered directly contacting with the layer.
About low-refraction compound (LRIC), the compound referred in experimental section is most preferred.
Organic electronic device of the invention can be organic electroluminescence device (OLED), illuminating device or organic effect
Transistor (OFET).Illuminating device can be any one of the device for illuminating, irradiating, signal or project.Their phases
It is classified as illumination, irradiation, signalling and projection device with answering.Illuminating device is usually made of following：Light irradiation source will irradiate
The device and these components are connected into individual devices and irradiation source and light is protected to pass that flux is transferred in space with required direction
Shell of the defeated system from damage and the influence of ambient enviroment.
Organic electroluminescence device according to the present invention may include more than one luminescent layer according to another aspect, excellent
Select two or three luminescent layers.OLED comprising more than one luminescent layer is also been described as tandem OLED or stepped construction
OLED。
Organic electroluminescence device (OLED) can be bottom emission device or top emission device.
On the other hand it is related to the device comprising at least one organic electroluminescence device (OLED).
Device comprising Organic Light Emitting Diode is, for example, display or illumination panel.
In the present invention, term defined below, these definition should be applied, unless in claims or this specification
In other places give different definition.
In the context of the present specification, term " different " related from material or " difference " refer to material in its structure
It is different in formula.
Term " OLED " and " Organic Light Emitting Diode " are used and are had the same meaning simultaneously.Art used herein
Language " organic electroluminescence device " may include Organic Light Emitting Diode and organic light-emitting transistor (OLET).
As used in this article, " weight percent ", " wt.-% ", " weight percent ", " weight % " and its variation shape
Formula refers to forming, component, substance or reagent are referenced as the component of respective electron transfer layer, the weight of substance or reagent
Divided by its respective total weight of electron transfer layer and multiplied by 100.It is appreciated that all groups of each electron transfer layer and electron injecting layer
Point, the total weight percent amount of substance and reagent be chosen so as to it no more than 100wt.-%.
As used in this article, " percent by volume ", " vol.-% ", " percent volume ", " volume % " and its variation shape
Formula refers to that the volume that composition, component, substance or reagent are referenced as to the component of respective electron transfer layer, substance or reagent is removed
With its respective total volume of electron transfer layer and multiplied by 100.It is appreciated that the totality of all components of cathode layer, substance and reagent
Product percentage is chosen so as to it no more than 100vol.-%.
Regardless of whether explicitly pointing out, it is believed that all numerical value is all modified by term " about " herein.As used herein
, term " about " refers to the quantity variation that can occur.Regardless of whether being modified by term " about ", claim all includes the number
The equivalent of amount.
It should be noted that as used in the specification and the appended claims, it is no except non-content is otherwise expressly specified
Then singular "one", "an" and " described " include plural reference.
Term " not having ", " not containing ", " not including " are not excluded for impurity.About present invention purpose achieved, impurity is not
With technical effect.
In the context of the present specification, term " not shining substantially " or " not shining " mean relative to visible luminescent light
Spectrum, compound or layer to the contribution of the visible luminescent spectrum from device less than 10%, preferably smaller than 5%.Visible luminescent spectrum
It is wavelength is about >=380nm to about≤780nm luminescent spectrum.
Preferably, n-type dopant and matrix compounds are substantially non-luminous or do not shine.
Operating voltage is also referred to as U, is in 10 milliamps per square centimeter of (mA/cm2) under with volt (V) measurement.
Candela/ampere efficiency is also referred to as cd/A efficiency, is in 10 milliamps per square centimeter of (mA/cm2) under with candela/
Amperometric measurement.
External quantum efficiency is also referred to as EQE, with percentage (%) measurement.
Color space is described by coordinate CIE-x and CIE-y (CIE 1931).For blue-light-emitting, CIE-y
It is especially important.Lesser CIE-y indicates deeper blue.
The also referred to as lowest unoccupied molecular orbital of the highest occupied molecular orbital of HOMO and also referred to as LUMO is with electron-volt
(eV) it measures.
Term " OLED ", " Organic Light Emitting Diode ", " organic luminescent device ", " organic optoelectronic device " and " organic hair
Optical diode " is used and is had the same meaning simultaneously.
Term " service life " and " service life " are used and are had the same meaning simultaneously.
Anode and cathode can be described as anode/cathode or anode/cathode or anode layer/cathode layer.
Room temperature is also referred to as environment temperature, is 23 DEG C.
Specific embodiment
The different low-index materials of different chemical property, i.e. OLED device have been tested in the context of the present invention
In ADD-1, ADD-3 and ADD-5.Particularly suitable some low-index materials are listed in the table below in 1 in the sense of the present invention.
Table 1：
Other compounds used in following device embodiments are shown in Table 2.
Table 2：
Determine the measurement method of the refractive index of performance enhancing layer.
The refractive index of performance enhancing layer is measured by ellipsometry.Used ellipsometer is by J.A.Woollam public affairs
Take charge of the M2000-UI that (USA) is provided, in 245-1690nm work in wavelength ranges, with horizontal base and 45 ° -90 ° from
Dynamic pilot angle.The layer and up to tens microns of thick films of sub-nanometer thickness can be measured.In order to consider film refractive index it is each
Anisotropy enhances silicon base (IES) using the interference of the silicon oxide layer on a silicon surface with 950nm.In detail, measurement is retouched
It is set forth in Guskova etc., J.Phys.Chem.C (physical chemistry periodical C) 2013,117,17285；D and Yokoyama etc.,
Appl.Phys.Lett. in (Applied Physics flash report) 2008,93,173302.
Table 3：Layer sequence in OLED device embodiment, the material, the thickness degree, concentration that use.
Table 3：
| Layer name | Title material | Concentration [weight %] | Thickness degree [nm] |
| Anode | ITO | 90 | |
| HIL | HTM-1:PD-1 | 3 | 10 |
| HTL-1 | HTM-1 | 110 | |
| HTL-2 | HTM-2 | 10 | |
| EML | Main body -1 or main body -2:Illuminator -1 or illuminator -2 | 3 | 20 |
| ETL-1 | ETM-1 | 10 | |
| EIIL | ETM-2:Yb | 5 | 0 or 5 |
| Performance enhancing layer | ETM-2:ADD-1 to ADD-4:ND-1 | Variation | 30 |
| Cathode | Al | 100 |
Table 4：Use LRIC ADD-3 and main body -1：The OLED device performance data of illuminator -1.Device is in performance enhancement
Layer and the upper difference of the material of electron injection middle layer composition.Comparative example does not have performance enhancing layer.By in performance enhancing layer with
Weight %43:47:10 concentration ratio uses ETM-2：Yb：ADD-3 and in electron injection middle layer with weight %95：5 it is dense
Degree is than using ETM-2：Yb realizes optimum efficiency in OLED 2 of the invention.When being measured relative to comparative example, without electricity
The OLED 4 of the invention of son injection middle layer efficiency under+6% loss of voltage also improves about+7%.
Table 4：
Table 5：Using LRIC ADD-1 and there is main body -1：The material group of illuminator -1 and performance enhancing layer becomes ETM-
2：Yb：ADD-1 is weight %62:28:10 OLED device performance data.Thickness degree is as shown in table 4.
Table 5：
Table 6：Using LRIC ADD-5 and there is main body -2：Illuminator -2 and the performance enhancement formed using different materials
The OLED device performance data of layer.Service performance enhancement layer forms ETM-2：Yb：ADD-5 is weight %42:57:1 present invention
OLED 6 obtains optimum performance.Thickness degree is as shown in table 4.
Table 6：
Table 7：Pass through the refractive index for the performance enhancing layer (PEL) of the invention that ellipsometry measures.
Table 7：
In the foregoing specification, disclosed feature is individually or any with its in detail in the claims and/or in the accompanying drawings
Combined form can be for realizing material of the invention in a variety of manners.
Claims (10)
1. organic electroluminescence device, the organic electroluminescence device include：First electrode, at least one second electrode, extremely
A few luminescent layer and at least one electron transporting zone, wherein the luminescent layer and the electron transporting zone be arranged in it is described
Between at least one second electrode and the first electrode, and the electron transporting zone is arranged in the luminescent layer and described
Between at least one second electrode, wherein at least one described electron transporting zone includes
A) the first electron transfer layer, first electron transfer layer preferably do not include n-type dopant；With
B) performance enhancing layer, the performance enhancing layer have≤1.6 refractive index at the wavelength of 1200nm；
Wherein
First electron transfer layer is arranged between the luminescent layer and the performance enhancing layer；And
The performance enhancing layer is arranged between first electron transfer layer and at least one described second electrode.
2. organic electroluminescence device according to claim 1, wherein the electron transporting zone also includes electron injection
Middle layer, wherein the electron injection middle layer is arranged between first electron transfer layer and the performance enhancing layer.
3. organic electroluminescence device according to claim 1 or 2, wherein the organic electroluminescence device is organic hair
Optical diode or organic electroluminescent transistor.
4. organic electroluminescence device according to any one of the preceding claims, wherein the performance enhancing layer includes
Low refraction material in silsesquioxane, alkane, perfluoro alkane, perfluoroalkyl phosphonic acids, perfluor phosphine oxide and metal fluoride
Material.
5. organic electroluminescence device according to claim 4, wherein the silsesquioxane is by general formula SixRxO1.5xTable
Show, wherein R is alkyl, the alkyl may include at least one be selected from B, Si, N, P, O and S hetero atom and/or may include at least
One be halogen atom substituent group；And x is selected from 6,8,10,12,14 and 16.
6. organic electroluminescence device according to claim 4 or 5, wherein the alkane, which is selected from, has 18 to 60 carbon originals
The alkane of son.
7. the organic electroluminescence device according to any one of claim 4 to 6, wherein the metal fluoride is selected from
Or mixtures thereof LiF, NaF, KF.
8. the organic electroluminescence device according to any one of claim 4 to 7, wherein the low refractive material is selected from
Or mixtures thereof LiF.
9. organic electroluminescence device according to any one of the preceding claims, wherein the performance enhancing layer also wraps
Containing n-type dopant, wherein the n-type dopant is selected from alkali metal, alkaline-earth metal, rare earth metal is alkali metal, alkaline-earth metal, dilute
The organic complex or alkali metal of earth metal, alkaline-earth metal, the halide of rare earth metal or the n-type dopant are under
The compound that one of formula indicates：
Or mixtures thereof.
10. organic electroluminescence device according to any one of the preceding claims, the organic electroluminescence device
Successively comprising first electrode, p-type doping hole transmission layer, the first optional hole transmission layer, the second optional hole transmission layer,
The luminescent layer, first electron transfer layer, the optional electron injection middle layer, the performance enhancing layer and it is described extremely
Few second electrode, wherein the electron injection middle layer can be n-type doping electron transfer layer.
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| WO2019139175A1 (en) * | 2018-01-09 | 2019-07-18 | Kyushu University, National University Corporation | Organic light-emitting field-effect transistor |
| CN111384254B (en) * | 2018-12-27 | 2021-09-14 | Tcl科技集团股份有限公司 | Quantum dot light-emitting diode |
| WO2022074499A1 (en) * | 2020-10-09 | 2022-04-14 | 株式会社半導体エネルギー研究所 | Light-emitting apparatus, electronic equipment, and illumination apparatus |
| WO2024023954A1 (en) * | 2022-07-27 | 2024-02-01 | シャープディスプレイテクノロジー株式会社 | Light-emitting element and display device |
Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060011067A (en) * | 2004-07-29 | 2006-02-03 | 삼성에스디아이 주식회사 | Organic electroluminescence device |
| CN101097996A (en) * | 2007-06-20 | 2008-01-02 | 中国科学院长春光学精密机械与物理研究所 | Organic phosphorescent electroluminescence device based on cuprous complex material |
| WO2009000237A1 (en) * | 2007-06-22 | 2008-12-31 | Novaled Ag | Use of a precursor of an n-dopant for doping an organic semiconductive material, precursor and electronic or optoelectronic component |
| CN101345292A (en) * | 2008-05-29 | 2009-01-14 | 清华大学 | Top-illuminating OLED display device and preparation method thereof |
| CN101359721A (en) * | 2008-09-23 | 2009-02-04 | 吉林大学 | Top radiation organic EL part with optical spectrum adjustable |
| US20090066234A1 (en) * | 2007-07-05 | 2009-03-12 | Hyun Sik Chae | Light emitting devices and compositions |
| CN101582440A (en) * | 2008-05-14 | 2009-11-18 | 精工爱普生株式会社 | Light emitting device and electronic apparatus |
| US20100063221A1 (en) * | 2006-12-01 | 2010-03-11 | Kaneka Corporation | Polysiloxane composition |
| CN102232081A (en) * | 2008-12-01 | 2011-11-02 | 巴斯夫欧洲公司 | Silsesquioxane photoinitiators |
| CN102468447A (en) * | 2010-11-18 | 2012-05-23 | 鸿富锦精密工业（深圳）有限公司 | Organic light-emitting diode |
| CN103180993A (en) * | 2010-11-09 | 2013-06-26 | 皇家飞利浦电子股份有限公司 | Organic electroluminescent device |
| US20140061601A1 (en) * | 2012-09-03 | 2014-03-06 | Lg Display Co., Ltd. | Anthracene compound and organic light emitting diode including the same |
| CN104183738A (en) * | 2013-05-24 | 2014-12-03 | 海洋王照明科技股份有限公司 | Organic electroluminescent device and preparation method thereof |
| KR20150075674A (en) * | 2013-12-26 | 2015-07-06 | 주식회사 엘지화학 | Organic light emitting device |
| US20150372258A1 (en) * | 2013-04-15 | 2015-12-24 | Canon Kabushiki Kaisha | Organic electroluminescence element, image-forming apparatus, display apparatus, and imaging apparatus |
| CN105409021A (en) * | 2013-07-29 | 2016-03-16 | 默克专利有限公司 | Electroluminescence device |
| EP3109916A1 (en) * | 2015-06-23 | 2016-12-28 | Novaled GmbH | Organic light emitting device comprising polar matrix, metal dopant and silver cathode |
| US20170117480A1 (en) * | 2015-10-27 | 2017-04-27 | Samsung Display Co., Ltd. | Organic electroluminescent device and display including the same |
| US20170133631A1 (en) * | 2014-07-24 | 2017-05-11 | Universal Display Corporation | Oled device having enhancement layer(s) |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100377321B1 (en) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | Electronic device comprising organic compound having p-type semiconducting characteristics |
| US6517958B1 (en) | 2000-07-14 | 2003-02-11 | Canon Kabushiki Kaisha | Organic-inorganic hybrid light emitting devices (HLED) |
| DE10357044A1 (en) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Process for doping organic semiconductors with quinonediimine derivatives |
| DE102004010954A1 (en) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Use of a metal complex as an n-dopant for an organic semiconductive matrix material, organic semiconductor material and electronic component |
| JP2007141736A (en) | 2005-11-21 | 2007-06-07 | Fujifilm Corp | Organic electroluminescent element |
| KR101361710B1 (en) | 2006-03-21 | 2014-02-10 | 노발레드 아게 | Method for preparing doped organic semiconductor materials and formulation utilized therein |
| EP1837926B1 (en) | 2006-03-21 | 2008-05-07 | Novaled AG | Heterocyclic radicals or diradicals and their dimers, oligomers, polymers, di-spiro and polycyclic derivatives as well as their use in organic semiconductor materials and electronic devices. |
| EP1837927A1 (en) | 2006-03-22 | 2007-09-26 | Novaled AG | Use of heterocyclic radicals for doping of organic semiconductors |
| EP3457451B1 (en) | 2007-04-30 | 2019-07-17 | Novaled GmbH | The use of oxocarbon, pseudooxocarbon and radialene compounds |
| JP5810504B2 (en) | 2010-10-18 | 2015-11-11 | Jnc株式会社 | Laminated body and method for producing the same |
| KR20120041460A (en) | 2010-10-21 | 2012-05-02 | 엘지디스플레이 주식회사 | Organic light emitting diode device |
| EP2722908A1 (en) | 2012-10-17 | 2014-04-23 | Novaled AG | Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs |
| JP2014096418A (en) | 2012-11-07 | 2014-05-22 | Idemitsu Kosan Co Ltd | Organic electroluminescent element and electronic device |
| KR102083434B1 (en) | 2013-09-04 | 2020-03-03 | 삼성디스플레이 주식회사 | Organic light emitting device and manufacturing method thereof |
| EP2887412B1 (en) | 2013-12-23 | 2016-07-27 | Novaled GmbH | Semiconducting material |
| EP2887416B1 (en) | 2013-12-23 | 2018-02-21 | Novaled GmbH | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
| KR102221106B1 (en) | 2014-01-17 | 2021-03-02 | 삼성디스플레이 주식회사 | Organic light-emitting Devices |
| JP2016033917A (en) | 2014-07-29 | 2016-03-10 | 富士フイルム株式会社 | All-solid type secondary battery, battery electrode sheet, method for manufacturing battery electrode sheet, solid electrolytic composition, method for manufacturing solid electrolytic composition, and method for manufacturing all-solid type secondary battery |
| US9859503B2 (en) | 2015-04-30 | 2018-01-02 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10381566B2 (en) * | 2015-06-17 | 2019-08-13 | National University Corporation Yamagata University | Organic charge transport layer, organic EL device, organic semiconductor device, and organic photoelectric device |
| EP3133663B1 (en) | 2015-08-18 | 2022-06-15 | Novaled GmbH | Metal amides for use as hole injection layer for an organic light-emitting diode (oled) |
| EP3133664A1 (en) | 2015-08-18 | 2017-02-22 | Novaled GmbH | Triaryl amine thick layer doped with metal amides for use as hole injection layer for an organic light-emitting diode (oled) |
| US10236461B2 (en) * | 2016-05-20 | 2019-03-19 | Samsung Electronics Co., Ltd. | Organic photoelectronic device and image sensor |
-
2017
- 2017-05-22 DE DE102017111137.9A patent/DE102017111137A1/en active Pending
-
2018
- 2018-05-18 US US15/983,197 patent/US11183649B2/en active Active
- 2018-05-21 KR KR1020180058009A patent/KR102578661B1/en active IP Right Grant
- 2018-05-22 CN CN201810495632.8A patent/CN108933197B/en active Active
Patent Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060011067A (en) * | 2004-07-29 | 2006-02-03 | 삼성에스디아이 주식회사 | Organic electroluminescence device |
| US20100063221A1 (en) * | 2006-12-01 | 2010-03-11 | Kaneka Corporation | Polysiloxane composition |
| CN101097996A (en) * | 2007-06-20 | 2008-01-02 | 中国科学院长春光学精密机械与物理研究所 | Organic phosphorescent electroluminescence device based on cuprous complex material |
| WO2009000237A1 (en) * | 2007-06-22 | 2008-12-31 | Novaled Ag | Use of a precursor of an n-dopant for doping an organic semiconductive material, precursor and electronic or optoelectronic component |
| US20100187515A1 (en) * | 2007-06-22 | 2010-07-29 | Novaled Ag | Use of a Precursor of an N-Dopant for Doping an Organic Semiconductive Material, Precursor and Electronic or Optoelectronic Component |
| US20090066234A1 (en) * | 2007-07-05 | 2009-03-12 | Hyun Sik Chae | Light emitting devices and compositions |
| CN101582440A (en) * | 2008-05-14 | 2009-11-18 | 精工爱普生株式会社 | Light emitting device and electronic apparatus |
| CN101345292A (en) * | 2008-05-29 | 2009-01-14 | 清华大学 | Top-illuminating OLED display device and preparation method thereof |
| CN101359721A (en) * | 2008-09-23 | 2009-02-04 | 吉林大学 | Top radiation organic EL part with optical spectrum adjustable |
| CN102232081A (en) * | 2008-12-01 | 2011-11-02 | 巴斯夫欧洲公司 | Silsesquioxane photoinitiators |
| US20120142793A1 (en) * | 2008-12-01 | 2012-06-07 | Basf Se | Silsesquioxane photoinitiators |
| US20130285027A1 (en) * | 2010-11-09 | 2013-10-31 | Koninklijke Philips Electronics N.V. | Organic electroluminescent device |
| CN103180993A (en) * | 2010-11-09 | 2013-06-26 | 皇家飞利浦电子股份有限公司 | Organic electroluminescent device |
| CN102468447A (en) * | 2010-11-18 | 2012-05-23 | 鸿富锦精密工业（深圳）有限公司 | Organic light-emitting diode |
| US20140061601A1 (en) * | 2012-09-03 | 2014-03-06 | Lg Display Co., Ltd. | Anthracene compound and organic light emitting diode including the same |
| US20150372258A1 (en) * | 2013-04-15 | 2015-12-24 | Canon Kabushiki Kaisha | Organic electroluminescence element, image-forming apparatus, display apparatus, and imaging apparatus |
| CN104183738A (en) * | 2013-05-24 | 2014-12-03 | 海洋王照明科技股份有限公司 | Organic electroluminescent device and preparation method thereof |
| CN105409021A (en) * | 2013-07-29 | 2016-03-16 | 默克专利有限公司 | Electroluminescence device |
| KR20150075674A (en) * | 2013-12-26 | 2015-07-06 | 주식회사 엘지화학 | Organic light emitting device |
| US20170133631A1 (en) * | 2014-07-24 | 2017-05-11 | Universal Display Corporation | Oled device having enhancement layer(s) |
| EP3109916A1 (en) * | 2015-06-23 | 2016-12-28 | Novaled GmbH | Organic light emitting device comprising polar matrix, metal dopant and silver cathode |
| US20170117480A1 (en) * | 2015-10-27 | 2017-04-27 | Samsung Display Co., Ltd. | Organic electroluminescent device and display including the same |
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| US20180337352A1 (en) | 2018-11-22 |
| KR20180127936A (en) | 2018-11-30 |
| KR102578661B1 (en) | 2023-09-13 |
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| CN108933197B (en) | 2023-10-24 |
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